Oxidative cleavage of 1,2-diols to give aldehydes/ketones

by James

Description: Treatment of vicinal diols (1,2-diols) with an oxidant such as NaIO4, HIO4, or Pb(OAc)4 cleaves C–C bonds and forms carbonyl compounds.
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My question is regarding Lead(IV) acetate. Does the initial compound have to have both a secondary and tertiary alcohol in order to have the reaction or can the reaction occur in the presence of just a tertiary or a secondary alcohol? In other words, could the reaction occur if the initial compound was a simple alkane with a secondary alcohol attached? Thank you! Your website and resources are fantastic and very helpful :D

Sodium periodate will do it, as will periodic acid. Ruthenium tetraoxide will do this too. Tin acetate is not an oxidant; copper acetate won’t do it; Iron acetate will not lead to this oxidation in the absence of other oxidants. One could maybe add hydrogen peroxide to the Fe(III), but then all hell would break loose.